Potent and selective farnesyl transferase inhibitors

J Med Chem. 2004 Dec 30;47(27):6812-20. doi: 10.1021/jm030502y.

Abstract

We recently described a novel series of CA(1)A(2)X peptidomimetics as farnesyl transferase inhibitors (FTIs). These compounds possess an N-(4-piperidinyl)benzamide scaffold mimicking A(1)A(2) residue. Extensive exploration of structure--activity relationships revealed that replacement of cysteine by substituted benzylimidazoles provided nanomolar FTIs with in vitro activities (18e, IC(50) = 4.60 nM on isolated enzyme, EC(50) = 20.0 nM for growth inhibition on a tumor cell line). The molecular docking of 18e and 19e in the active site of the enzyme provided details of key interactions with the protein and showed that the methionine or phenylalanine residue fits into the aryl binding site.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkyl and Aryl Transferases / antagonists & inhibitors*
  • Animals
  • Binding Sites
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology
  • Farnesyltranstransferase
  • Humans
  • Mice
  • NIH 3T3 Cells
  • Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • Alkyl and Aryl Transferases
  • Farnesyltranstransferase